This invention relates to the synthesis and use of certain compounds as fly attractants. The compounds may be substituted with acceptable attraction qualities for known compounds which require expensive and complicated synthesis.
The compound cis-9-tricosene was reported by Carlson et al. (Science, volume 174, page 76 (1971)) to be an effective attractant for male houseflies. Carlson et al. synthesized the compound by a Wittig reaction of nonanal with the product of phenyllithium and tetradecyltriphenylphosphonium bromide. The trans isomer of cis-9-tricosene was a minor byproduct of the synthesis. Carlson and Beroza (Environmental Entomol., Volume 2, page 555 (1979)) showed that the cis compound could attract male and female houseflies to sticky traps or poison-baited food traps in field tests and thus could be used as an aid in controlling fly populations. Carlson et al. (J. Agr. Food Chem., Volume 22, page 194 (1974)) showed that hydrocarbon analogs of cis-9-tricosene which had longer or shorter carbon skeltons were not as effective at attracting flies.
Other syntheses of cis-9-tricosene have been reported. Cargill and Rosenblum (J. Org. Chem., Volume 37, page 3971 (1972); U.S. Pat. No. 3,798,273) reported a synthesis by reaction of erucic acid with methyllithium, followed by Wolff-Kishner reduction. Ho and Wong (Can. J. Chem., Volume 52, page 1923 (1974)) have also reported a synthesis involving an olefinic acid and an organolithium compound, as well as by a procedure involving a Grignard reagent and an olefinic acid chloride. An electrolytic procedure has been used by Gribble et al. (J. Chem. Soc. Chem. Commun., page 735 (1973)) and by Meresz and Mosgai et al. (Can. Entomol., Volume 104, page 1963 (1972); U.S. Pat. No. 4,018,844).
All of the previous procedures for synthetic fly attractant synthesis have one or more of the following requirements which add to the cost or difficulty of synthesis: inert atmospheres, anhydrous solvents, organometallic reagents, electrolytic conditions, or contamination by byproducts. Therefore, the need exists for the synthesis of novel compounds which avoid complicated synthesizing requirements but retain acceptable fly attractant qualities.